These are the players who won the most money in their respective seasons on Jeopardy! in regular-season play.
Fleming era (1964–1975; 1978–1979)[]
| Rank | Season | Name | TW (Regular-season play excluding consolation prizes + adjusted values) |
★ |
|---|---|---|---|---|
| 1 | 6 | Jane Gschwend | $8,250 | 5 |
| 2 | 3 | Burns Cameron | $7,070 | |
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Syndicated era (1984–present)[]
| Rank | Season | Name | TW (Regular-season play excluding consolation prizes + adjusted values) |
★ |
|---|---|---|---|---|
| 1 | 21 | Ken Jennings | $2,520,700 | 74 |
| 2 | 35 | James Holzhauer | $2,462,216 | 32 |
| 3 | 38 | Matt Amodio | $1,518,601 | 38 |
| 4 | 39 | Cris Pannullo | $748,286 | 21 |
| 5 | 36 | Jason Zuffranieri | $532,496 | 19 |
| 6 | 41 | Scott Riccardi | $455,000 | 16 |
| 7 | 22 | David Madden | $430,400 | 19 |
| 8 | 30 | Julia Collins | $428,100 | 20 |
| 9 | 32 | Matt Jackson | $411,612 | 13 |
| 10 | 34 | Austin Rogers | $411,000 | 12 |
| 11 | 42 | Harrison Whitaker | $373,999 | 14 |
| 12 | 40 | Adriana Harmeyer | $349,600 | 15 |
| 13 | 33 | Seth Wilson | $265,002 | 12 |
| 14 | 27 | Tom Nissley | $235,405 | 8 |
| 15 | 24 | Larissa Kelly | $222,597 | 6 |
| 16 | 28 | Jason Keller | $213,900 | 9 |
| 17 | 20 | Tom Walsh | $184,900 | 7 |
| 18 | 31 | Greg Seroka | $180,401 | |
| 19 | 29 | Ben Ingram | $176,534 | 8 |
| 20 | 37 | Brian Chang | $163,904 | 7 |
| 21 | 25 | Justin Bernbach | $155,001 | |
| 22 | 19 | Brian Weikle | $149,200 | 5 |
| 23 | 26 | Jason Zollinger | $148,404 | 6 |
| 24 | 23 | Mehrun Etebari | $128,100 | 5 |
| 25 | 6 | Frank Spangenberg | $102,597 | |
| 26 | 18 | Eric Floyd | $97,800 | 4 |
| 27 | 8 | Jerome Vered | $96,801 | 5 |
| 28 | 11 | David Siegel | $86,200 | |
| 29 | 16 | Doug Lach | $85,400 | |
| 30 | 7 | Mark Born | $82,899 | |
| 31 | 10 | John Cuthbertson | $82,400 | |
| 32 | 14 | Dan Melia | $75,600 | |
| 33 | 17 | Babu Srinivasan | $75,100 | |
| 34 | 2 | Chuck Forrest | $72,800 | |
| 35 | 12 | Paul Thompson | $72,199 | |
| 36 | 9 | Ed Schiffer | $65,903 | |
| 37 | 4 | Bruce Naegeli | $64,200 | |
| 38 | 13 | Kim Worth | $64,000 | 4 |
| 39 | 5 | Brian Wangsgard | $62,398 | 5 |
| 40 | 3 | John Ryan | $61,800 | |
| 41 | 15 | David Bagley | $56,900 | 4 |
| 42 | 1 | Paul Boymel | $56,200 | 5 |
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